Theses and Dissertations

Date of Award

8-1-2024

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

First Advisor

Debasish Bandyopadhyay

Second Advisor

Jose Gutierrez-Gonzales

Third Advisor

K. Christopher Smith

Abstract

Four-membered cyclic amides, commonly known as β-lactams, have played a crucial role in drug discovery research since its discovery by Alexander Fleming in 1928 from Penicillium notatum. The β-lactam antibiotics are broadly effective against several bacterial infections through acylating the transpeptidase involved in cross-linking peptides to form peptidoglycan or periplasmic murein, which is a fundamental constituent of the bacterial cell wall for both the gram-positive (ten or more layers) and gram-negative (one or two layers) bacteria. Although for more than eight decades, β-lactams have been recognized as antibiotics, later, other medicinal activities of β-lactam derivatives have been reported, including lowering of high cholesterol levels, antidiabetic, and anticancer. On the other hand, synthesizing the spiro carbon center is challenging due to enormous steric hindrances and angular strain. As a part of our ongoing research on synthesizing pharmacologically relevant spiro compounds, herein we report the synthesis of spiro-centered β-lactams following the Staudinger [2+2] ketene-imine cycloaddition reaction. A small series of diversely substituted spiro-centered β-lactams has been synthesized and characterized by several spectroscopic techniques, including IR, NMR (one and two-dimensional NMR), and HRMS. Some of these spiro-β-lactams may be beneficial in future drug discovery research.

Comments

Copyright 2024 Nneoma James. https://proquest.com/docview/3116515990

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